What should I do with my life? Three approaches

Time to read this post: 9 minutes (yes it's a longer one)

Last week I was sitting in my office that overlooks Times Square in New York when I got a phone call from the CFO of one of the largest global food & drinks companies. He wanted some urgent career advice about a new job opportunity that had come his way and he didn’t know how to evaluate it. He had ten minutes.

Backing up for a moment, over the last few years I have worked with hundreds of professionals helping them to try and answer the question “what should I do with my life?”. Some of these conversations resulted in dramatic realizations; and others… well, not so much. I have noticed that each person seems to struggle with one of three large issues. This is a quick attempt to outline the three approaches to tackling these issues. These are fleshed out notes from a speech I gave last month.  Hopefully they make sense without the PowerPoint slides.

[A quick aside: back in 2004 I signed up with the Coaches Training Institute to train in the art of life coaching. It comprised six long weekends in a stuffy hotel room. Picture a twenty eight year old in a room full of unhappy overweight ladies who all want to help people for a living. We did trust falls and everything. I learned that life coaches are very well-intentioned, most struggle to make a decent living and that I should scuttle back to strategy consulting as fast as I could.]

However I made a resolution that if anyone ever asked me for a career conversation that I would say yes, no matter how busy I was. If you asked me to summarize what people are struggling with I would say:

Struggle 1: “I don’t know what I like or what I’m good at”. These folks tend not to have reflected on what they have enjoyed or succeeded at in the past.

Struggle 2: “I don’t know who I want to be when I grow up”. People in this category can’t make career decisions because they don’t have a clear end in mind. They tend to keep themselves busy so they don’t have to think about it.

Struggle 3: “I quite like what I’m doing but I worry that I’m just drifting”. These people tend to be quite content but worry that they will end up having a mediocre and somewhat undistinguished career.

Of course we all wrestle with each of these to some extent for all our lives. I recommend thinking about yourself & your career with three time perspectives. There is nothing profound about this but it tends to be quite helpful:

The past - What you have done in your life to date? Who you have been? What have been your highs & lows in your journey so far?
The present – Where are you right now? What’s working for you? Where are you stuck?
The future – What it is you are trying to do? Who is it you are trying to become?

The Past: reflect on your history

Part of the answer is in looking backwards and understanding how you got to where you are today. Most people in their rush to advance, resist looking in the rearview mirror. After all aren’t we all supposed to have no regrets? We all need to understand what it is that gives us energy and in what do we have experience in. I have written about this before and about being good at things you don’t enjoy. Here’s a useful matrix:

Simple ideas:
- reflecting with friends, family and colleagues and asking questions like “When have you seen me get most energized about work? What did you notice?”
- online strengths-diagnostics surveys like one that comes with the Strengthsfinder 2.0 book.
- glancing through your hard drive of old projects and work you’ve done. Look in email folders to prompt you to think about different work experiences
- Take a family photo album off the shelf and flip through it. Recall times when you’ve really enjoyed life or accomplished the most (and also times that you have been miserable or really struggled)

The Future: write the end of the story

We all face the luxury of unprecedented choices with our lives. We are the most overqualified, most educated, luckiest generation in history. We can do anything, go anywhere and we don’t have to follow in our parents’ footsteps. And yet this freedom turns out to be a terrible burden. Psychologists call it the Paradox of Choice. It’s a real problem. There is likely no single future perfect job that is sitting in a classified advert waiting for you to browse over a Sunday morning coffee.

The people who love what they do tend to have actively experimented. They didn’t know exactly what ‘it’ was. Instead they dreamed up three of four future selves that they could get excited about. Personally I can imagine being a business school professor, or running an online education company, or writing comedy screenplays. These are all future selves that I can get excited about. And I need to find ways to experiment with each to see if they are compelling careers or just nonsense that I’ve made up in my head.

So far, so obvious. Here are some tips that I’ve seen executive coaches use to help people understand who it is they could become:
- Write 3 x 200 word eulogies. One from the perspective of a business colleague, another from a member of your community, another from a friend or spouse. This is a slightly better exercise that writing your own obituary since is will focus you more on who you aspire to be versus what you would like to accomplish and be known for.
- Ask friends: “what do you see me doing in ten years time?”; often what’s obvious to them is not to us.
- Reread any past essays when you have written about your hopes & ambitions. Dig out those business school applications
- Try and answer the question: ‘what would I do if I knew I couldn’t fail?’

The Present: what's your story?

In our rush to over-achieve, we are all at risk of forever rushing to the next meeting, jumping on the next flight, replying to the never ending emails. We forget to pause, check in on ourselves and ask: are we remembering to enjoy the journey?

We have a deep need for life to make sense. We need to have a story that helps us connect the dots to the past and future. We need a sense of coherence that explains where we are coming from and how that connects to where we are heading. This is about having a personal narrative. In the story of our lives we are the protagonist. So the question is: are you living a good story?

I’ll save the detail for now, but we can learn a lot from great literature and movies about what we as humans like in a good story. Then we can apply those lessons to our own lives. Do we want to live an epic quest? Are we in a romantic comedy? Or is it a recurring tragedy? Unless we have a sense of where we are in the story of our lives, it is no surprise when we feel unsettled or adrift.

Tips include:
- Keep a journal, noting down highs & lows. When on a long flight or commute, take 5 minutes to reflect where your current work could unexpectedly take you
- Which movies or book characters do you most admire? What would you need to do to live your life more like them? What would they do in your situation?
- Write down your life story to date in the form of a movie plot.
- The next time someone asks you “What do you do?” try out a new story, come up with a response that intrigues the other person. Tell them you are considering changing careers, or taking up an unusual hobby, or moving to Africa. See where the conversation takes you and what ideas it gives you.

I have come to believe that this final approach – finding our own compelling narrative, is the hardest to get my head around. It’s also the one that I struggle to articulate in writing. The chapter in Working Identity by Hermina Ibarra on sense-making is very good:  Working Identity: Unconventional Strategies for Reinventing Your Career

Anyway, where was I?  When I speak with people about their career strategy, they normally can identify if their issue is with the past, present or future (or some combination).  We can then focus in on what it is they need to do to move forward.  And the CFO of the global food company?  For him it was about understanding his past.  He needed to understand his strengths and areas of expertise.  What was the most useful thing he said he did after we spoke?  Well he told me it was leafing through all family photo albums reflecting on different parts of his life and spotting patterns with regard to what energised him.
Tough questions
- Which of the three approaches (past, present & future) is most relevant to you?
- What story are you living? Do you have a clear narrative of where you are in your own life story?